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The Finkelstein Reaction: Quantitative Reaction Kinetics of an SN2 Reaction Using Nonaqueous Conductivity

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R. David Pace and Yagya Regmi

Department of Science and Mathematics, Lyon College, Batesville, AR 72503

J. Chem. Educ., 2006, 83 (9), p 1344

DOI: 10.1021/ed083p1344

Publication Date (Web): September 1, 2006

Section:

History, Education, and Documentation

Abstract

Two essential concepts for students to grasp in the undergraduate organic chemistry sequence are substitution chemistry and elimination chemistry (S_N1/S_N2 and E1/E2). However, students are often confounded by the seemingly endless series of structure–reactivity relationships. This dualistic relationship of conceptual essentialness and student confusion usually results in a line of demarcation for many second-year organic chemistry students. It is at this point that students either pull together the fundamental structure–reactivity relationships and go on to draw relevant mechanistic conclusions that underpin the balance of their organic chemistry experience or the flood of material washes over them and they wind up in a miserable struggle to keep their heads above water until the end of the spring semester. Therefore, we have developed a quantitative kinetics laboratory exercise featuring the Finkelstein reaction (S_N2) for use in the first-semester organic chemistry course that utilizes nonaqueous conductivity as the method by which relevant structure–temperature–solvent effects are examined.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Calibration

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

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  Journal of Chemical Education2009 86 (7), 850
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A Safer, Discovery-Based Nucleophilic Substitution Experiment
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- A Safer, Discovery-Based Nucleophilic Substitution Experiment
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  Journal of Chemical Education2009 86 (3), 363
  A discovery-based nucleophilic substitution experiment is described in which students compare the reactivity of chloride and iodide ions in an SN2 reaction. This experiment improves upon the well-known "Competing Nucleophiles" experiment in that it does ...
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